Town of Pine Plains Rentals
From $3253 per night (USD)VRBO
The Entire Estate at Picardy Farms
- Bedrooms:
- 7
- Bathrooms:
- 10
- Sleeps:
- 20
Enjoy complete privacy across this 10-acre estate, perfect for retreats, large gatherings, or peaceful escapes. You'll ...
From $3253 per night (USD)VRBO
From $369 per night (USD)VRBO
Hudson Valley - Picardy Farm: The Barn
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The bright and cozy Barn has just been renovated and is part of the Picardy Farm, surrounded by an idyllic pastoral set ...
From $369 per night (USD)VRBO
From $426 per night (USD)VRBO
Hudson Valley - Picardy Farm: The Garden House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This impressive Bright and Sunny 3 Bedroom and 2.5 bath home is comfortable and quiet. With 2 queen bedrooms, 2 single b ...
From $426 per night (USD)VRBO
From $1053 per night (USD)VRBO
PRIVATE 65 ACRE ESTATE - POOL, TENNIS, PICKLEBALL, 4BR\nBOOK JULY OR AUG 2026 NOW
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
A bucolic retreat, this completely secluded estate, nestled on over 50 acres, offering your exclusive use of on site ac ...
From $1053 per night (USD)VRBO
From $947 per night (USD)VRBO
A Country Lodge Straight Out of the Pages of a Great Novel
- Bedrooms:
- 0
- Bathrooms:
- 4
- Sleeps:
- 12
The Lodge Imagine a country lodge straight out of the pages of a great novel. Rustic chic combines with modern ameniti ...
From $947 per night (USD)VRBO
From $1035 per night (USD)Expedia
Secluded and Spectacular Views
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
The Silo Set on 700 acres of wooded Hudson Valley real estate, The Silo is reached by crossing a bridge over a flowing ...
From $1035 per night (USD)Expedia
From $229 per night (USD)VRBO
Adorable secret hideaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
The Nook (Silo garage apartment) This adorable secret hideaway is a self-contained efficiency apartment set in the mids ...
From $229 per night (USD)VRBO
From $612 per night (USD)Expedia
Mid-Century Home Surrounded by Meadows
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Hideaway This mid-century modern home reigns over a magical world in the heart of New York State’s historic Hudson ...
From $612 per night (USD)Expedia
From $204 per night (USD)VRBO
Stylish Pine Plains Home Near Parks & Hiking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Small town charm meets modern convenience at this updated home in Pine Plains! With 1 bedroom, 1 bathroom, and a fully e ...
From $204 per night (USD)VRBO
From $905 per night (USD)Expedia
Enchanting cottage in a private oasis
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Newly renovated cottage located at Ingadi Farmhouse, a family owned and run farm situated on 127 acres of land in the Hu ...
From $905 per night (USD)Expedia
From $365 per night (USD)VRBO
rural, serene + sophisticated space
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
In the country, yet short drives to the Hudson River Valley's towns. So many guests have a hard time leaving to go out ...
From $365 per night (USD)VRBO
From $386 per night (USD)Expedia
Twin Island Lake House • Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hudson Valley’s best kept secret. Built in 2018, perched on 4 acres. 3 bedrooms 2 full baths include master suite with p ...
From $386 per night (USD)Expedia
From $3441 per night (USD)VRBO
The Farm House w. Garden Cottage at Picardy Farms
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 8
Welcome to The Farm House, a spacious 1830 Greek Revival landmark residence at Picardy Farms. This lovingly restored 1 ...
From $3441 per night (USD)VRBO
From $508 per night (USD)VRBO
The Cabin-A quiet get away for rest and relaxation
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Quiet escape from the world. The Cabin settles into its surroundings with deceptive subtlety, while inside it is surpris ...
From $508 per night (USD)VRBO
From $247 per night (USD)VRBO
Vintage 50's lake cabin featured in Fresh Cottage Magazine's 'dream retreats'
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Rustic cabin by Twin Island Lake, Pine Plains, NY Sitting on quiet Lake Road and nestled in the woods, my rental built i ...
From $247 per night (USD)VRBO
From $1654 per night (USD)VRBO
Elegant Historic Hudson Valley Gilded Age Mansion On 4+ Parklike Acres
- Bedrooms:
- 9
- Bathrooms:
- 9
- Sleeps:
- 22
The Pines includes a gourmet eat-in kitchen, butler's pantry, formal dining room, music room, library/game room, mud roo ...
From $1654 per night (USD)VRBO
From $331 per night (USD)VRBO
Lakefront Designer House in Pine Plains, NY.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Lakefront property at its finest, recently renovated designer house. Beautiful Twin Island Lake. The peace and tranquill ...
From $331 per night (USD)VRBO
From $406 per night (USD)VRBO
Tanner Farmhouse - Rural Cozy Escape
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Experience the charm of Tanner Farmhouse, a rustic yet modern home in Pine Plains, NY. This meticulously renova ...
From $406 per night (USD)VRBO
From $253 per night (USD)VRBO
the suite @ barn & bike - private, bucolic, serene setting
- Bedrooms:
- 0
- Bathrooms:
- 1
- Sleeps:
- 2
A 675 sq ft. fully private suite with your own entrance in an early American eyebrow colonial. The well appointed space ...
From $253 per night (USD)VRBO
From $1254 per night (USD)VRBO
The Library Retreat: 3 Building Estate w/Pool+Pond
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 12
Summary: Discover "The Library Retreat," a captivating multi-farmhouse in Pine Plains, just 2 hours from NYC. Set on a v ...
From $1254 per night (USD)VRBO
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Historic Cottage w Brand New Hot Tub and Game Room
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Restored 1810 cottage where historic charm meets modern living. Follow and tag us on IG @theupstatecub! Welcom ...
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From $760 per night (USD)Expedia
The George is an elegant restored home in the Hudson Valley
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
The George is a beautiful perfectly restored turn of the century home in the heart of Hudson Valley horse country. On a ...
From $760 per night (USD)Expedia
From $493 per night (USD)VRBO
Family home by Polo fields with great yard & game rm. EV charger, pet friendly!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Renovated & charming 3BR, 2BA home with spacious yard situated across from Mashomack Polo fields in the picturesque Huds ...
From $493 per night (USD)VRBO
From $466 per night (USD)Expedia
Lakeside Peninsula Escape
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Wake up to stunning views at this lakefront guest house on a private peninsula in Pine Plains, New York. Enjoy the lake ...
From $466 per night (USD)Expedia
From $1105 per night (USD)VRBO
Post & Beam • Stunningly Designed Luxury Home w/ Pool & Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the immaculate and professionally-designed post & beam rental home of two New York creatives, including the F ...
From $1105 per night (USD)VRBO
From $734 per night (USD)Expedia
Willow Vale • Stunningly Designed Historical Icon w/ Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our historic & meticulously restored home, Willow Vale, situated on a quiet & idyllic country road and nestle ...
From $734 per night (USD)Expedia
From $1168 per night (USD)VRBO
Upstate Mountain View Retreat
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 11
Escape to this stunning mountain retreat in Dutchess County. This spacious home comfortably accommodates up to 10 guest ...
From $1168 per night (USD)VRBO
From $1174 per night (USD)Expedia
Historic 5BR Colonial Retreat in the Heart of the Hudson Valley
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Step into the comfort of country living with designer flair at this beautifully restored 1775 Colonial—a private and spa ...
From $1174 per night (USD)Expedia
From $842 per night (USD)VRBO
Pool & Private Acreage: Luxe Hudson Valley Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Picture Windows w/ Views | Family Friendly | Backyard Bonfire Space Deer wandering the yard, golden sunsets, and starry ...
From $842 per night (USD)VRBO